Synthesis of 2,4-disubstituted pyrroles by rearrangements of 2-furanyl carbamates

Sezgin Kiren; Xuechuan Hong; Carolyn A Leverett; Albert Padwa

doi:10.1021/ol900059e

Synthesis of 2,4-disubstituted pyrroles by rearrangements of 2-furanyl carbamates

Org Lett. 2009 Mar 19;11(6):1233-5. doi: 10.1021/ol900059e.

Authors

Sezgin Kiren¹, Xuechuan Hong, Carolyn A Leverett, Albert Padwa

Affiliation

¹ Department of Chemistry, Emory University, Atlanta, Georgia, 30322, USA.

PMID: 19231853
DOI: 10.1021/ol900059e

Abstract

2,4-Disubstituted pyrroles were synthesized by an oxidative rearrangement of a furanyl carbamate followed by sequential reaction of the resulting 5-methoxypyrrol-2(5H)-one with different alkyl lithiates. The final step of the procedure involves heating the ring opened 1-methoxy-5-oxopentylcarbamate with a primary amine.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Carbamates / chemistry*
Catalysis
Furans / chemistry*
Molecular Structure
Oxidation-Reduction
Pyrroles / chemical synthesis*
Pyrroles / chemistry

Substances

Carbamates
Furans
Pyrroles